142329-23-5

Basic information

• Product Name: 6-fluorobenzo[b]thiophene-2-carboxylic acid
• Synonyms: 6-fluorobenzo[b]thiophene-2-carboxylic acid;6-Fluoro-1-benzothiophene-2-carboxylic acid, 2-Carboxy-6-fluorobenzo[b]thiophene
• CAS NO: 142329-23-5
• Molecular Formula: C₉H₅FO₂S
• Molecular Weight: 196.1982032
• Mol File: 142329-23-5.mol
• Article Data: 10

Chemical Properties

• Boiling Point: 379.4°C at 760 mmHg
• Flash Point: 183.2°C
• Appearance: /
• Density: 1.511g/cm³
• Vapor Pressure: 1.98E-06mmHg at 25°C
• Refractive Index: 1.686
• CAS DataBase Reference: 6-fluorobenzo[b]thiophene-2-carboxylic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 6-fluorobenzo[b]thiophene-2-carboxylic acid(142329-23-5)
• EPA Substance Registry System: 6-fluorobenzo[b]thiophene-2-carboxylic acid(142329-23-5)

Safety Data

• Hazardous Substances Data: 142329-23-5(Hazardous Substances Data)

Usage

General Description

"6-fluorobenzo[b]thiophene-2-carboxylic acid" is a specialized aryl organic compound. The "6-fluoro" part indicates the presence of a fluorine atom, while "benzo[b]thiophene" is a fused-ring system combining a benzene ring with a thiophene (a ring with four carbon atoms and a sulfur atom). The "2-carboxylic acid" signifies the presence of a carboxylic acid group, a key functional group in organic chemistry involved in various chemical reactions, occupying the second position on the thiophene ring. This chemical is primarily used in advanced organic synthesis and pharmaceutical applications thanks to its particular set of chemical reactivity and properties.

InChI:InChI=1/C9H5FO2S/c10-6-2-1-5-3-8(9(11)12)13-7(5)4-6/h1-4H,(H,11,12)

Upstream product

• 212078-68-7 6-fluorobenzo[b]thiophene-2-carboxylic acid ethyl ester 
• 1550-35-2 2,4-difluorobenzaldehyde 
• 181765-32-2 3-(4-fluorophenyl)-2-mercapto-2-propenoic acid 
• 550998-52-2 6-fluorobenzo[b]thiophene-2-carboxylic acid methyl ester 

Downstream Products

• 205055-10-3 6-fluoro-benzo[b]thiophene 
• 212078-69-8 1-(6-fluorobenzo[b]thiophen-2-yl)-3-(1-triphenylmethyl-1H-imidazol-4-yl)-propan-1-ol 

Relevant articles and documents

Design, synthesis, and biological activity evaluation of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives as broad-spectrum antifungal agents

To discover antifungal compounds with broad-spectrum and stable metabolism, a series of 2-(benzo[b]thiophen-2-yl)-4-phenyl-4,5-dihydrooxazole derivatives was designed and synthesized. Compounds A30-A34 exhibited excellent broad-spectrum antifungal activity against Candida albicans with MIC values in the range of 0.03–0.5 μg/mL, and against Cryptococcus neoformans and Aspergillus fumigatus with MIC values in the range of 0.25–2 μg/mL. In addition, compounds A31 and A33 showed high metabolic stability in human liver microsomes in vitro, with the half-life of 80.5 min and 69.4 min, respectively. Moreover, compounds A31 and A33 showed weak or almost no inhibitory effect on the CYP3A4 and CYP2D6. The pharmacokinetic evaluation in SD rats showed that compound A31 had suitable pharmacokinetic properties and was worthy of further study.

Discovery of fluorescent coumarin-benzo[b]thiophene 1, 1-dioxide conjugates as mitochondria-targeting antitumor STAT3 inhibitors

STAT3 has been extensively studied as a potential antitumor target. Though studies on regulating STAT3 mainly focus on the inhibition of STAT3 phosphorylation at Tyr705 residue, the phosphorylation at Ser727 residue of STAT3 protein is also closely associated with the mitochondrial import of STAT3 protein. N, N-diethyl-7-aminocoumarin is a fluorescent mitochondria-targeting probe. In this study, a series of STAT3 inhibitors were developed by connecting N, N-diethyl-7-aminocoumarin fluorophore with benzo [b]thiophene 1, 1-dioxide moiety. All designed compounds displayed potent anti-proliferative activity against cancer cells. The representative compound 7a was mainly accumulated in mitochondria visualized by its fluorescence. STAT3 phosphorylation was inhibited by compound 7a at both Tyr705 and Ser727 residues. Compound 7a inhibited STAT3 phosphorylation whereas had no influence on the phosphorylation levels of STAT1, JAK2, Src and Erk1/2, indicating good selectivity of compound 7a. Moreover, compound 7a down-regulated the expression of STAT3 target genes Bcl-2 and Cyclin D1, increased ROS production and remarkably reduced the mitochondrial membrane potential to induce mitochondrial apoptotic pathway. Furthermore, compound 7a in vivo suppressed breast cancer 4T1 implanted tumor growth. Taken together, these results highlighted that compound 7a might be a promising mitochondria-targeting STAT3 inhibitor for cancer therapy.

Reinvestigating Old Pharmacophores: Are 4-Aminoquinolines and Tetraoxanes Potential Two-Stage Antimalarials?

The syntheses and antiplasmodial activities of various substituted aminoquinolines coupled to an adamantane carrier are described. The compounds exhibited pronounced in vitro and in vivo activity against Plasmodium berghei in the Thompson test. Tethering a fluorine atom to the aminoquinoline C(3) position afforded fluoroaminoquinolines that act as intrahepatocytic parasite inhibitors, with compound 25 having an IC50 = 0.31 μM and reducing the liver load in mice by up to 92% at 80 mg/kg dose. Screening our peroxides as inhibitors of liver stage infection revealed that the tetraoxane pharmacophore itself is also an excellent liver stage P. berghei inhibitor (78: IC50 = 0.33 μM). Up to 91% reduction of the parasite liver load in mice was achieved at 100 mg/kg. Examination of tetraoxane 78 against the transgenic 3D7 strain expressing luciferase under a gametocyte-specific promoter revealed its activity against stage IV-V Plasmodium falciparum gametocytes (IC50 = 1.16 ± 0.37 μM). To the best of our knowledge, compounds 25 and 78 are the first examples of either an 4-aminoquinoline or a tetraoxane liver stage inhibitors.